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Identification
NameFluvastatin
Accession NumberDB01095  (APRD00346)
TypeSmall Molecule
GroupsApproved
Description

Fluvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reductase catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Fluvastatin belongs to a class of medications called statins and is used to reduce plasma cholesterol levels and prevent cardiovascular disease. It is also the first entirely synthetic HMG-CoA reductase inhibitor and is structurally distinct from the fungal derivatives of this therapeutic class.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluvastatin Sodium ERtablet, extended release80 mg/1oralSandoz Inc2015-10-162016-04-05Us
Lescolcapsule20 mg/1oralNovartis Pharmaceuticals Corporation1993-12-302016-04-23Us
Lescolcapsule40 mg/1oralPhysicians Total Care, Inc.2002-03-082016-04-05Us
Lescolcapsule20 mg/1oralPhysicians Total Care, Inc.1994-06-102016-04-05Us
Lescolcapsule40 mg/1oralNovartis Pharmaceuticals Corporation1993-12-302016-04-23Us
Lescol 20mgcapsule20 mgoralNovartis Pharmaceuticals Canada Inc1994-12-31Not applicableCanada
Lescol 40mgcapsule40 mgoralNovartis Pharmaceuticals Canada Inc1994-12-31Not applicableCanada
Lescol XLtablet, extended release80 mg/1oralCarilion Materials Management2000-10-062016-04-05Us
Lescol XLtablet, extended release80 mg/1oralPhysicians Total Care, Inc.2002-03-122016-04-05Us
Lescol XLtablet (extended-release)80 mgoralNovartis Pharmaceuticals Canada Inc2004-04-05Not applicableCanada
Lescol XLtablet, extended release80 mg/1oralNovartis Pharmaceuticals Corporation2000-10-062016-04-23Us
Sandoz Fluvastatincapsule40 mgoralSandoz Canada Incorporated2013-02-15Not applicableCanada
Sandoz Fluvastatincapsule20 mgoralSandoz Canada Incorporated2013-02-15Not applicableCanada
Teva-fluvastatincapsule40 mgoralTeva Canada Limited2012-12-11Not applicableCanada
Teva-fluvastatincapsule20 mgoralTeva Canada Limited2012-12-11Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluvastatincapsule20 mg/1oralTeva Pharmaceuticals USA Inc2012-07-052016-04-23Us
Fluvastatincapsule40 mg/1oralTeva Pharmaceuticals USA Inc2012-07-052016-04-23Us
Fluvastatin Sodiumcapsule40 mg/1oralCarilion Materials Management2013-03-192016-04-05Us
Fluvastatin Sodiumcapsule20 mg/1oralCarilion Materials Management2013-03-192016-04-05Us
Fluvastatin Sodiumcapsule40 mg/1oralMylan Pharmaceuticals Inc.2013-03-192016-04-23Us
Fluvastatin Sodiumcapsule20 mg/1oralMylan Pharmaceuticals Inc.2013-03-192016-04-23Us
Fluvastatin Sodiumtablet, film coated, extended release80 mg/1oralMylan Pharmaceuticals Inc.2015-09-112016-04-23Us
Over the Counter ProductsNot Available
International Brands
NameCompany
CanefAstraZeneca
CranocAstellas
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Fluvastatin Sodium
Thumb
  • InChI Key: ZGGHKIMDNBDHJB-UHFFFAOYNA-M
  • Monoisotopic Mass: 433.166531173
  • Average Mass: 433.4478
DBSALT000088
Categories
UNII4L066368AS
CAS number93957-54-1
WeightAverage: 411.4659
Monoisotopic: 411.18458653
Chemical FormulaC24H26FNO4
InChI KeyInChIKey=FJLGEFLZQAZZCD-NDDZYTDBNA-N
InChI
InChI=1/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/s2
IUPAC Name
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
SMILES
CC(C)N1C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C2=CC=CC=C12)C1=CC=C(F)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 3-phenylpyrrole
  • Medium-chain hydroxy acid
  • Indole or derivatives
  • Indole
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Halogenated fatty acid
  • Halobenzene
  • Fluorobenzene
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:38565 )
Pharmacology
IndicationTo be used as an adjunct to dietary therapy to prevent cardiovascular events. May be used as secondary prevention in patients with coronary heart disease (CHD) to reduce the risk of requiring coronary revascularization procedures, for reducing progression of coronary atherosclerosis in hypercholesterolemic patients with CHD, and for the treatment of primary hypercholesterolemia and mixed dyslidipidemia.
PharmacodynamicsFluvastatin, the first synthetically-derived HMG-CoA reductase inhibitor, is a hydrophilic, acidic, antilipemic agent used to lower cholesterol and triglyceride levels associated with primary hypercholesterolemia and mixed dyslipidemia (Fredrickson types IIa and IIb), to slow the progression of coronary atherosclerosis in patients with CHD and as secondary prevention therapy in patients with CHD to reduce the risk of requiring coronary revascularization procedures. Although similar to lovastatin, simvastatin, and pravastatin, fluvastatin has a shorter half-life, no active metabolites, extensive protein binding, and minimal CSF penetration. Fluvastatin acts primarily in the liver. It is prepared as a racemate of two erythro enantiomers of which the 3R,5S enantiomer exerts the pharmacologic effect.
Mechanism of actionFluvastatin selectively and competitively inhibits the hepatic enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reductase is responsible for converting HMG-CoA to mevalonate, the rate-limiting step in cholesterol biosynthesis. Inhibition results in a decrease in hepatic cholesterol levels which stimulates the synthesis of LDL receptors and increases hepatic uptake of LDL cholesterol. The end result is decreased levels of plasma total and LDL cholesterol.
Related Articles
AbsorptionRapidly and almost completely absorbed (> 90%), but undergoes extensive first pass metabolism. Bioavailability is 24% (range 9-50%) when a 10 mg dose is given. The mean relative bioavailability of the extended-release tablet is 29% (range: 9% to 66%) compared to an immediate-release capsule administered under fasting conditions. When given orally, fluvastatin reaches peak concentrations (Tmax) in less than one hour. Taking the extended release tablet with a high-fat meal will delay absorption (Tmax = 6 hours) and increase bioavailability by approximately 50%. However, the maximum concentration of fluvastatin sodium extended-release tablets seen after a high fat meal is less than the peak concentration following a single dose or twice daily dose of the 40 mg fluvastatin capsule.
Volume of distribution
  • 0.35 L/kg
Protein binding98% bound to plasma proteins. At therapeutic concentrations, the protein binding of fluvastatin is not affected by warfarin, salicylic acid and glyburide.
Metabolism

Undergoes hepatic metabolism primarily via hydroxylation of the indole ring at the 5- and 6-positions to 5-hydroxy fluvastatin and 6-hydroxy fluvastatin, respectively. N-dealkylation to N-desisopropyl fluvastatin and beta-oxidation of the side chain also occurs. Metabolized primarily by the CYP2C9 isozyme system (75%), and to a lesser extent by CYP3A4 (~20%) and CYP2C8 (~5%). Hydroxylated metabolites retain some pharmcological activity, but are present as conjugates (glucuronides and sulfates) in the blood and are rapidly eliminated via bile into feces. Both enantiomers of fluvastatin are metabolized in a similar manner. Fluvastatin also undergoes glucuronidation via UGT enzymes.

SubstrateEnzymesProduct
Fluvastatin
6-HydroxyfluvastatinDetails
Fluvastatin
N-Deisopropyl-fluvastatinDetails
Fluvastatin
5-HydroxyfluvastatinDetails
Route of eliminationWhen orally administered, fluvastatin is primarily excreted in the faces ( ~90%) as metabolites, with less than 2% present as unchanged drug. Approximately 5% was recovered in the urine.
Half life3 hours
Clearance
  • 0.8 L/h/kg
  • 107 ± 38.1 L/h [Hypercholesterolemia patients receiving a single dose of 20 mg]
  • 87.8 ± 45 L/h [Hypercholesterolemia patients receiving 20 mg twice daily]
  • 108 ± 44.7 L/h [Hypercholesterolemia patients receiving 40 mg single]
  • 64.2 ± 21.1 L/h [Hypercholesterolemia patients receiving 40 mg twice daily]
ToxicityGenerally well-tolerated. May cause gastrointestinal upset (diarrhea, nausea, constipation, gas, abdominal pain), myotoxicity (mypothy, myositis, rhabdomyolysis), and hepatotoxicity.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Fluvastatin Action PathwayDrug actionSMP00119
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5053
P-glycoprotein substrateNon-substrate0.5176
P-glycoprotein inhibitor INon-inhibitor0.7395
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterNon-inhibitor0.8823
CYP450 2C9 substrateNon-substrate0.7305
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6111
CYP450 1A2 substrateNon-inhibitor0.6003
CYP450 2C9 inhibitorNon-inhibitor0.675
CYP450 2D6 inhibitorNon-inhibitor0.8983
CYP450 2C19 inhibitorNon-inhibitor0.6314
CYP450 3A4 inhibitorNon-inhibitor0.8811
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.809
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7909
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9472 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9899
hERG inhibition (predictor II)Non-inhibitor0.848
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, film coated, extended releaseoral80 mg/1
Capsuleoral20 mg/1
Capsuleoral40 mg/1
Capsuleoral20 mg
Capsuleoral40 mg
Tablet (extended-release)oral80 mg
Tablet, extended releaseoral80 mg/1
Prices
Unit descriptionCostUnit
Lescol XL 80 mg 24 Hour tablet4.25USD tablet
Lescol xl 80 mg tablet4.24USD tablet
Lescol xl 80 mg tablet sa3.66USD tablet
Lescol 20 mg capsule3.38USD capsule
Lescol 40 mg capsule3.37USD capsule
Lescol Xl 80 mg Extended-Release Tablet1.62USD tablet
Lescol 40 mg Capsule1.35USD capsule
Lescol 20 mg Capsule0.96USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2085037 No2000-11-282012-12-10Canada
CA2346868 No2008-09-092019-10-12Canada
US5354772 No1994-10-112011-10-11Us
US6242003 Yes2000-10-132020-10-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point194-197 °CNot Available
water solubility0.46 mg/LNot Available
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00441 mg/mLALOGPS
logP3.69ALOGPS
logP3.83ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.69 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.86 m3·mol-1ChemAxon
Polarizability43.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Gustavo Frenkel, Eyal Gilboa, “Process for the preparation of fluvastatin sodium crystal form XIV.” U.S. Patent US20050119342, issued June 02, 2005.

US20050119342
General References
  1. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817 ]
External Links
ATC CodesC10AA04
AHFS Codes
  • 24:06.08
PDB EntriesNot Available
FDA labelDownload (84.5 KB)
MSDSDownload (101 KB)
Interactions
Drug Interactions
Drug
AcipimoxAcipimox may increase the myopathic rhabdomyolysis activities of Fluvastatin.
Aluminum hydroxideThe serum concentration of Fluvastatin can be decreased when it is combined with Aluminum hydroxide.
AmiodaroneThe metabolism of Fluvastatin can be decreased when combined with Amiodarone.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Fluvastatin.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Fluvastatin.
AtazanavirThe serum concentration of Fluvastatin can be increased when it is combined with Atazanavir.
BezafibrateBezafibrate may increase the myopathic rhabdomyolysis activities of Fluvastatin.
BoceprevirThe serum concentration of Fluvastatin can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Fluvastatin.
Calcium carbonateThe serum concentration of Fluvastatin can be decreased when it is combined with Calcium carbonate.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Fluvastatin.
CholestyramineThe serum concentration of Fluvastatin can be decreased when it is combined with Cholestyramine.
CiprofibrateThe risk or severity of adverse effects can be increased when Ciprofibrate is combined with Fluvastatin.
ColchicineColchicine may increase the myopathic rhabdomyolysis activities of Fluvastatin.
CyclosporineThe serum concentration of Fluvastatin can be increased when it is combined with Cyclosporine.
Cyproterone acetateThe serum concentration of Fluvastatin can be increased when it is combined with Cyproterone acetate.
DaclatasvirThe serum concentration of Fluvastatin can be increased when it is combined with Daclatasvir.
DaptomycinThe risk or severity of adverse effects can be increased when Fluvastatin is combined with Daptomycin.
DicoumarolFluvastatin may increase the anticoagulant activities of Dicoumarol.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Fluvastatin.
EltrombopagThe serum concentration of Fluvastatin can be increased when it is combined with Eltrombopag.
EtravirineThe serum concentration of Fluvastatin can be decreased when it is combined with Etravirine.
FenofibrateThe risk or severity of adverse effects can be increased when Fenofibrate is combined with Fluvastatin.
FluconazoleThe serum concentration of Fluvastatin can be increased when it is combined with Fluconazole.
FosphenytoinThe serum concentration of Fluvastatin can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe risk or severity of adverse effects can be increased when Fusidic Acid is combined with Fluvastatin.
GemfibrozilGemfibrozil may increase the myopathic rhabdomyolysis activities of Fluvastatin.
LanthanumThe serum concentration of Lanthanum can be decreased when it is combined with Fluvastatin.
Magnesium oxideThe serum concentration of Fluvastatin can be decreased when it is combined with Magnesium oxide.
MifepristoneThe serum concentration of Fluvastatin can be increased when it is combined with Mifepristone.
NiacinThe risk or severity of adverse effects can be increased when Niacin is combined with Fluvastatin.
NicotinamideThe risk or severity of adverse effects can be increased when Nicotinamide is combined with Fluvastatin.
PazopanibFluvastatin may increase the hepatotoxic activities of Pazopanib.
PhenytoinThe serum concentration of Fluvastatin can be decreased when it is combined with Phenytoin.
RaltegravirRaltegravir may increase the myopathic rhabdomyolysis activities of Fluvastatin.
RifabutinThe serum concentration of Fluvastatin can be decreased when it is combined with Rifabutin.
RitonavirThe serum concentration of Fluvastatin can be increased when it is combined with Ritonavir.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Fluvastatin.
TelaprevirThe serum concentration of Fluvastatin can be increased when it is combined with Telaprevir.
TeriflunomideThe serum concentration of Fluvastatin can be increased when it is combined with Teriflunomide.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Fluvastatin.
TrabectedinFluvastatin may increase the myopathic rhabdomyolysis activities of Trabectedin.
Food Interactions
  • May be taken with or without food, but should be taken consistently.
  • When given with an evening meal, Cmax and AUC decreased while Tmax increased 2-fold

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Nadph binding
Specific Function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular Weight:
97475.155 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Podar K, Tai YT, Hideshima T, Vallet S, Richardson PG, Anderson KC: Emerging therapies for multiple myeloma. Expert Opin Emerg Drugs. 2009 Mar;14(1):99-127. doi: 10.1517/14728210802676278 . [PubMed:19249983 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574 ]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817 ]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292 ]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Kivisto KT, Niemi M, Schaeffeler E, Pitkala K, Tilvis R, Fromm MF, Schwab M, Eichelbaum M, Strandberg T: Lipid-lowering response to statins is affected by CYP3A5 polymorphism. Pharmacogenetics. 2004 Aug;14(8):523-5. [PubMed:15284534 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574 ]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817 ]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292 ]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Fischer V, Johanson L, Heitz F, Tullman R, Graham E, Baldeck JP, Robinson WT: The 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor fluvastatin: effect on human cytochrome P-450 and implications for metabolic drug interactions. Drug Metab Dispos. 1999 Mar;27(3):410-6. [PubMed:10064574 ]
  2. Toda T, Eliasson E, Ask B, Inotsume N, Rane A: Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009 Nov;105(5):327-32. doi: 10.1111/j.1742-7843.2009.00453.x. Epub 2009 Aug 6. [PubMed:19663817 ]
  3. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292 ]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Cohen LH, van Leeuwen RE, van Thiel GC, van Pelt JF, Yap SH: Equally potent inhibitors of cholesterol synthesis in human hepatocytes have distinguishable effects on different cytochrome P450 enzymes. Biopharm Drug Dispos. 2000 Dec;21(9):353-64. [PubMed:11523064 ]
  2. Scripture CD, Pieper JA: Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81. [PubMed:11368292 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. http://www.pharmacologyweekly.com/content/pages/ugt-enzymes-medications-herbs-substrate-inhibitor-inducer
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 Da
References
  1. http://www.pharmacologyweekly.com/content/pages/ugt-enzymes-medications-herbs-substrate-inhibitor-inducer
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. http://www.pharmacologyweekly.com/content/pages/ugt-enzymes-medications-herbs-substrate-inhibitor-inducer

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular Weight:
77402.175 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Kopplow K, Letschert K, Konig J, Walter B, Keppler D: Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8. Epub 2005 Jul 26. [PubMed:16046661 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Ekins S, Johnston JS, Bahadduri P, D'Souza VM, Ray A, Chang C, Swaan PW: In vitro and pharmacophore-based discovery of novel hPEPT1 inhibitors. Pharm Res. 2005 Apr;22(4):512-7. Epub 2005 Apr 7. [PubMed:15846457 ]
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Drug created on June 13, 2005 07:24 / Updated on April 30, 2016 03:10